3-aryl-pyrrolidine-2,4-dione derivatives

ABSTRACT

New 3-arylpyrrolidine-2,4-dione derivatives of the formula (I): ##STR1## in which the variables A, B, E, R, X, Y, Z and n are set forth in the specification, are useful as insecticides, acaricides, and herbicides.

This is a Continuation-in-Part of application Ser. No. 07/652,348, filedFeb. 7, 1991, now abandoned.

The invention relates to new 3-aryl-pyrrolidine-2,4-dione derivatives,to a plurality of processes for their preparation, and to their use asinsecticides, acaricides and herbicides.

Pharmaceutical properties have previously been described for3-acyl-pyrrolidine-2,4-diones (S. Suzuki et. al. Chem. Pharm. Bull. 151120 (1967)). N-Phenyl-pyrrolidine-2,4-diones were furthermoresynthesized by R. Schmierer and H. Mildenberger Liebigs Ann. Chem. 19851095. A biological activity of these compounds was not described.

EP-A 0,262,399 discloses compounds of a similar structure(3-aryl-pyrrolidine-2,4-diones), but no herbicidal, insecticidal oracaricidal action has been disclosed for these compounds.

New 3-arylpyrrolidine-2,4-dione derivatives have now been found, whichare illustrated by the formula (I) ##STR2## in which A representsoptionally halogen-substituted alkyl, alkenyl, alkinyl, alkoxyalkyl,polyalkoxyalkyl, alkylthioalkyl or cycloalkyl which is optionallyinterrupted by hetero atoms, or represents arylalkyl which is optionallysubstituted by halogen, alkyl, halogenoalkyl, alkoxy or nitro,

B and E independently of one another represent hydrogen, alkyl oralkoxyalkyl or

A and B, together with the nitrogen or carbon atom to which they arebonded, form a cyclic ring which can be interrupted by hetero atoms orgroups of hetero atoms,

X represents alkyl, halogen or alkoxy,

Y represents hydrogen, alkyl, halogen, alkoxy or halogenoalkyl,

Z represents alkyl, halogen or alkoxy,

n represents a number from 0-3,

R represents the groups ##STR3## in which L and M represent oxygen orsulphur,

R¹, R² and R³ independently of one another represent alkyl, alkoxy,alkylamino, dialkylamino, alkylthio, alkenylthio, alkinylthio orcycloalkylthio, each of which is optionally substituted by halogen, andrepresent phenyl, benzyl, phenoxy or phenylthio, each of which isoptionally substituted,

R⁴ and R⁵ independently of one another represent hydrogen, or representalkyl, alkenyl, alkoxy or alkoxyalkyl, each of which is optionallysubstituted by halogen, or represent optionally substituted phenyl, orrepresent optionally substituted benzyl, or R⁴ and R⁵ together representan alkylene radical which is optionally interrupted by oxygen,

R⁶ represents alkyl which is optionally substituted by halogen and whichcan be interrupted by oxygen, or represents phenyl which is optionallysubstituted by halogen, halogenoalkyl or alkoxy, or represents benzylwhich is optionally substituted by halogen, halogenoalkyl, alkyl andalkoxy, or represents alkenyl or alkinyl,

as well as the pure enantiomeric forms of compounds of the formula (I).

Taking into account the various meanings (a), (b), (c) and (d) of thegroup R of the general formula (I), the following main structures (Ia)to (Id) result: ##STR4## where A, B, E, L, M, X, Y, Z_(n), R¹, R², R³,R⁴, R⁵ and R⁶ have the abovementioned meanings.

Furthermore, it has been found that 3-aryl-pyrrolidine-2,4-diones of theformula (Ia) ##STR5## in which A, B, E, L, X, Y, Z, R¹, R² and n havethe abovementioned meaning, are obtained when

A) 3-aryl-pyrrolidine-2,4-diones of the formula (II) or their enols##STR6## in which A, B, E, X, Y, Z and n have the abovementioned meaningare reacted with phosphorus compounds of the general formula (III)##STR7## in which L, R¹ and R² have the abovementioned meaning and

Hal represents halogen, in particular chlorine and bromine, ifappropriate in the presence of a diluent, if appropriate in the presenceof an acid-binding agent and if appropriate in the presence of a phasetransfer catalyst.

B) Furthermore, it has been found that compounds of the formula (Ib)##STR8## in which A, B, E, X, Y, Z, R³ and n have the abovementionedmeaning are obtained when compounds of the formula (II) ##STR9## inwhich A, B, E, X, Y, Z and n have the abovementioned meaning are reactedwith sulphonyl chlorides of the general formula (IV)

    R.sup.3 --SO.sub.2 --Cl                                    (IV)

in which

R³ has the abovementioned meaning, if appropriate in the presence of adiluent and if appropriate in the presence of an acid-binding agent.

C) Furthermore, it has been found that compounds of the formula (Ic)##STR10## in which A, B, E, L, X, Y, Z, R⁴, R⁵ and n have theabove-mentioned meaning are obtained when compounds of the formula (II)##STR11## in which A, B, E, X, Y, Z and n have the abovementionedmeaning

α) are reacted with isocyanates of the general formula (V)

    R.sup.4 --N═C═O                                    (V)

in which

R⁴ has the abovementioned meaning, if appropriate in the presence of adiluent and if appropriate in the presence of a catalyst,

β) are reacted with carbamoyl chlorides or thiocarbamoyl chlorides ofthe general formula (VI) ##STR12## in which L, R⁴ and R⁵ have theabovementioned meaning, if appropriate in the presence of a diluent andif appropriate in the presence of an acid-binding agent.

D) Furthermore, it has been found that compounds of the formula (Id)##STR13## in which A, B, E, L, M, R⁶, X, Y, Z and n have theabove-mentioned meaning are obtained when compounds of the formula (II)##STR14## in which A, B, E, X, Y, Z and n have the abovementionedmeaning are reacted

α) with chloromonothioformic esters, chloroformic thioesters orchlorodithioformic esters of the general formula VII ##STR15## in whichL, M and R⁶ have the abovementioned meaning, if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent, or

β) with carbon disulphide and subsequently with alkyl halides of thegeneral formula VIII

    R.sup.6 --Hal                                              (VIII)

in which

R⁶ has the abovementioned meaning and Hal represents chlorine, bromineor iodine.

E) Furthermore, it has been found that compounds of the formula (Ie)##STR16## in which R, X, Y, Z and n have the abovementioned meaning,

E represents hydrogen and

A' and B' together represent --CH₂ --CH₂ --SO--CH₂ --, --CH₂ --SO--CH₂--CH₂ -- or CH₂ --SO--CH₂ -- are obtained when compounds of the formula(If) ##STR17## in which R, X, Y, Z and n have the abovementionedmeaning,

E represents hydrogen and

A" and B" together represent --CH₂ --CH₂ --S--CH₂ --, --CH₂ --S--CH₂--CH₂ -- or --CH₂ --S--CH₂ -- are reacted with approximately equimolaramounts of an oxidant, if appropriate in the presence of a diluent.

F) Furthermore, it has been found that compounds of the formula (Ig)##STR18## in which R, X, Y, Z and n have the abovementioned meaning,

E represents hydrogen and

A'" and B'" together represent --CH₂ --CH₂ --SO₂ --CH₂ --, --CH₂ --SO₂--CH₂ --CH₂ -- or --CH₂ --SO₂ --CH₂ -- are obtained when compounds ofthe formula (If) ##STR19## in which R, X, Y, Z and n have theabovementioned meaning,

E represents hydrogen and

A" and B" together represent --CH₂ --CH₂ --S--CH₂ --, --CH₂ --S--CH₂--CH₂ -- or --CH₂ --S--CH₂ --, are reacted with at least twice theequimolar amounts of an oxidant, if appropriate in the presence of adiluent.

Surprisingly, it has been found that the new 3-arylpyrrolidine-2,4-dionederivatives of the formula (I) are distinguished by outstandinginsecticidal, acaricidal and herbicidal actions.

Preferred 3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I)are those in which

A represents optionally halogen-substituted straight-chain or branchedC₁ -C₁₂ -alkyl, C₃ -C₈ -alkenyl, C₃ -C₈ -alkinyl, C₁ -C₁₀ -alkoxy-C₂ -C₈-alkyl, C₁ -C₈ -polyalkoxy-C₂ -C₈ -alkyl, C₁ -C₁₀ -alkylthio-C₂ -C₈-alkyl, cycloalkyl which has 3-8 ring atoms and which can be interruptedby oxygen and/or sulphur, or represents aryl-C₁ -C₆ -alkyl which isoptionally substituted by halogen, C₁ -C₆ -alkyl-C₁ -C₆ -haloalkyl, C₁-C₆ -alkoxy or nitro,

B and E independently of one another represent hydrogen orstraight-chain or branched C₁ -C₁₂ -alkyl or C₁ -C₈ -alkoxyalkyl, or

A and B together with the nitrogen or carbon atom to which they arebonded form a 4 to 8-membered cyclic ring which can be interrupted by asulphur atom or a sulphoxide or a sulphonyl group,

X represents C₁ -C₆ -alkyl, halogen or C₁ -C₆ -alkoxy,

Y represents hydrogen, C₁ -C₆ -alkyl, halogen, C₁ -C₆ -alkoxy or C₁ -C₃-halogenoalkyl,

Z represents C₁ -C₆ -alkyl, halogen or C₁ -C₆ -alkoxy,

n represents a number from 0-3,

R represents the groups ##STR20## in which L and M in each caserepresent oxygen or sulphur,

R¹, R² and R³ independently of one another represent C₁ -C₈ -alkyl, C₁-C₈ -alkoxy, C₁ -C₈ -alkylamino, di-(C₁ -C₈)-alkylamino, C₁ -C₈-alkylthio, C₂ -C₅ -alkenylthio, C₂ -C₅ -alkinylthio or C₃ -C₇-cycloalkylthio, each of which is optionally substituted by halogen, orrepresent phenyl, benzyl, phenoxy or phenylthio, each of which isoptionally substituted by halogen, nitro, cyano, C₁ -C₄ -alkoxy, C₁ -C₄-halogenoalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -halogenoalkylthio, C₁ -C₄-alkyl or C₁ -C₄ -halogenoalkyl,

R⁴ and R⁵ independently of one another represent C₁ -C₂₀ -alkyl, C₁ -C₂₀-alkoxy, C₂ -C₈ -alkenyl or C₁ -C₂₀ -alkoxy-C₁ -C₂₀ -alkyl, each ofwhich is optionally substituted by halogen, or represent phenyl which isoptionally substituted by halogen, C₁ -C₂₀ -halogenoalkyl, C₁ -C₂₀-alkyl or C₁ -C₂₀ -alkoxy, or represent benzyl which is optionallysubstituted by halogen, C₁ -C₂₀ -alkyl, C₁ -C₂₀ -halogenoalkyl or C₁-C₂₀ -alkoxy, or together represent a C₂ -C₆ -alkylene ring which isoptionally interrupted by oxygen,

R⁶ represents C₁ -C₂₀ -alkyl which is optionally substituted by halogenand which can be interrupted by oxygen, or represents phenyl which isoptionally substituted by halogen, C₁ -C₂₀ -halogenoalkyl or C₁ -C₂₀-alkoxy, or represents benzyl which is optionally substituted byhalogen, C₁ -C₂₀ -halogenoalkyl or C₁ -C₂₀ -alkoxy, or represents C₂ -C₈-alkenyl, or represents C₂ -C₅ -alkinyl,

as well as the pure enantiomeric forms of compounds of the formula (I).

Particularly preferred compounds of the formula (I) are those in which

A represents optionally halogen-substituted straight-chain or branchedC₁ -C₁₀ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkinyl, C₁ -C₈ -alkoxy-C₂ -C₈-alkyl, C₁ -C₆ -polyalkoxy-C₂ -C₆ -alkyl, C₁ -C₈ -alkylthio-C₂ -C₆-alkyl, cycloalkyl which has 3-7 ring atoms and which can be interruptedby 1-2 oxygen and/or sulphur atoms, or represents aryl-C₁ -C₄ -alkylwhich is optionally substituted by halogen , C₁ -C₄ -alkyl, C₁ -C₄-haloalkyl-C₁ -C₄ -alkoxy or nitro,

B and E independently of one another represent hydrogen orstraight-chain or branched C₁ -C₁₀ -alkyl or C₁ -C₆ -alkoxyalkyl, or

A and B together with the nitrogen or carbon atom to which they arebonded form a 4-to 7-membered cycle which can be interrupted by asulphur atom, or by a sulphoxide or sulphonyl group,

X represents C₁ -C₄ -alkyl, halogen or C₁ -C₄ -alkoxy,

Y represents hydrogen, C₁ -C₆ -alkyl, halogen, C₁ -C₄ -alkoxy or C₁ -C₂-halogenoalkyl,

Z represents C₁ -C₄ -alkyl, halogen or C₁ -C₄ -alkoxy,

n represents a number from 0-3,

R represents the groups ##STR21## in which L and M in each caserepresent oxygen or sulphur,

R¹, R² and R³ independently of one another represent C₁ -C₆ -alkyl, C₁-C₆ -alkoxy, C₁ -C₆ -alkylamino, di-(C₁ -C₆)-alkylamino, C₁ -C₆-alkylthio, C₃ -C₄ -alkenylthio, C₂ -C₄ -alkinylthio or C₃ -C₆-cycloalkylthio, each of which is optionally substituted by halogen, orrepresent phenyl, benzyl, phenoxy or phenylthio, each of which isoptionally substituted by fluorine, chlorine, bromine, nitro, cyano, C₁-C₃ -alkoxy, C₁ -C₃ -halogenoalkoxy, C₁ -C₃ -alkylthio, C₁ -C₃-halogenoalkylthio, C₁ -C₃ -alkyl or C₁ -C₃ -halogenoalkyl,

R⁴ and R⁵ independently of one another represent C₁ -C₂₀ -alkyl, C₁ -C₂₀-alkoxy, C₂ -C₈ -alkenyl or C₁ -C₂₀ -alkoxy-C₁ -C₂₀ -alkyl, each ofwhich is optionally substituted by halogen, or represent phenyl which isoptionally substituted by halogen, C₁ -C₅ -halogenoalkyl, C₁ -C₅ -alkylor C₁ -C₅ -alkoxy, or represent benzyl which is optionally substitutedby halogen, C₁ -C₅ -alkyl, C₁ -C₅ -halogenoalkyl or C₁ -C₅ -alkoxy,

R⁶ represents C₁ -C₂₀ -alkyl which is optionally substituted by halogenand which can be interrupted by oxygen, or represents phenyl which isoptionally substituted by halogen, C₁ -C₅ -halogenoalkyl or C₁ -C₅-alkoxy, or represents benzyl which is optionally substituted byhalogen, C₁ -C₅ -halogenoalkyl or C₁ -C₅ -alkoxy,

as well as the pure enantiomeric forms of compounds of the formula (I).

Particularly preferred compounds of the formula (I) are those in which

A represents optionally halogen-substituted straight-chain or branchedC₁ -C₈ -alkyl, C₃ -C₄ -alkenyl, C₃ -C₄ -alkinyl, C₁ -C₆ -alkoxy-C₂ -C₄-alkyl, C₁ -C₄ -polyalkoxy-C₂ -C₄ -alkyl, C₁ -C₆ -alkylthio-C₂ -C₄-alkyl, cycloalkyl which has 3-6 ring atoms and which can be interruptedby 1-2 oxygen and/or sulphur atoms, or represents aryl-C₁ -C₃ -alkylwhich is optionally substituted by fluorine, chlorine, bromine, methyl,ethyl, propyl, iso-propyl, methoxy, ethoxy, trifluoromethyl or nitro,

B and E independently of one another represent hydrogen orstraight-chain or branched C₁ -C₈ -alkyl or C₁ -C₄ -alkoxyalkyl, or

A and B together with the nitrogen or carbon atom to which they arebonded form a 5-6-membered cyclic ring which can be interrupted by asulphur atom or by a sulphoxide or sulphonyl group,

X represents methyl, ethyl, propyl, i-propyl, fluorine, chlorine,bromine, methoxy or ethoxy,

Y represents hydrogen, methyl, ethyl, propyl, i-propyl, butyl, i-butyl,tert.-butyl, fluorine, chlorine, bromine, methoxy, ethoxy ortrifluoromethyl,

Z represents methyl, ethyl, i-propyl, butyl, i-butyl, tert.-butyl,fluorine, chlorine, bromine, methoxy or ethoxy,

n represents a number from 0-3,

R represents the groups ##STR22## in which L and M in each caserepresent oxygen or sulphur,

R¹, R² and R³ independently of one another represent C₁ -C₄ -alkyl, C₁-C₄ -alkoxy, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)amino or C₁ -C₄-alkylthio, each of which is optionally substituted by fluorine orchlorine, or represent phenyl, benzyl, phenoxy or phenylthio, each ofwhich is optionally substituted by fluorine, chlorine, bromine, nitro,cyano, C₁ -C₂ -alkoxy, C₁ -C₄ -fluoroalkoxy, C₁ -C₂ -chloroalkoxy, C₁-C₂ -alkylthio, C₁ -C₂ -fluoroalkylthio, C₁ -C₂ -chloroalkylthio or C₁-C₃ -alkyl,

R⁴ and R⁵ independently of one another represent C₁ -C₁₀ -alkyl, C₁ -C₁₀-alkoxy or C₁ -C₁₀ -alkoxy-(C₁ -C₁₀)alkyl, each of which is optionallysubstituted by fluorine, chlorine or bromine, or represent phenyl whichis optionally substituted by fluorine, chlorine, bromine, C₁ -C₂₀-halogenoalkyl, C₁ -C₂₀ -alkyl or C₁ -C₄ -alkoxy, or represent benzylwhich is optionally substituted by fluorine, chlorine, bromine, C₁ -C₄-alkyl, C₁ -C₄ -halogenoalkyl or C₁ -C₄ -alkoxy,

R⁶ represents C₁ -C₁₀ -alkyl which is optionally substituted byfluorine, chlorine or bromine and which can be interrupted by oxygen, orrepresents phenyl which is optionally substituted by fluorine, chlorine,bromine, C₁ -C₄ -halogenoalkyl or C₁ -C₄ -alkoxy, or represents benzylwhich is optionally substituted by fluorine, chlorine, bromine, C₁ -C₄-halogenoalkyl or C₁ -C₄ -alkoxy,

as well as the pure enantiomeric forms of compounds of the formula (I).

If, according to process (A),3-(2,4,6-trimethylphenyl)-1,5-trimethylene-2,4-pyrrolidine-dione and2,2,2-trifluoroethyl methanethio-chlorophosphonate are used as startingmaterials, the course of the reaction can be illustrated by thefollowing equation: ##STR23##

If, according to process (B),3-(2,4,6-trimethylphenyl)-1,5-trimethylene-2,4-pyrrolidine-dione andmethanesulphonyl chloride are used as starting materials, the course ofthe reaction can be illustrated by the following equation: ##STR24##

If, according to process (C.sub.α)3-(2,4,6-trimethylphenyl)-1,5-trimethylene-2,4-pyrrolidine-dione andethyl isocyanate are used as starting materials, the course of thereaction can be illustrated by the following equation: ##STR25##

If, according to process (C.sub.β),3-(2,4,6-trimethylphenyl)-1,5-trimethylene-2,4-pyrrolidine-dione anddimethylcarbamoyl chloride are used as starting materials, the course ofthe reaction can be illustrated as follows: ##STR26##

If, according to process (D.sub.α),3-(2,4,6-trimethylphenyl)-1,5-tetramethylene-2,4-pyrrolidine-dione andmethyl chloromonothioformate are used as starting materials, the courseof the reaction can be illustrated as follows: ##STR27##

If, according to process (D.sub.β),3-(2,4,6-trimethylphenyl)-1,5-tetramethylene-2,4-pyrrolidine-dione,carbon disulphide and methyl iodide are used as starting components, thecourse of the reaction can be illustrated as follows: ##STR28##

Process (E) can be illustrated as follows: ##STR29##

Process (F) can be illustrated as follows: ##STR30##

The compounds of the formula (II) ##STR31## in which A, B, E, X, Y, Zand n have the abovementioned meaning and which are required as startingsubstances in the above processes (A)-(D), are new. For example,compounds of the formula (II) are obtained when N-acylamino acid estersof the formula (IX) ##STR32## in which A, B, E, X, Y, Z and n have theabovementioned meaning and

R⁷ represents alkyl are subjected to intramolecular condensation in thepresence of a diluent and in the presence of a base.

Some of the compounds of the formula (IX) ##STR33## in which A, B, E, X,Y, Z, n and R⁷ have the abovementioned meaning and which are required asstarting substances in the above process, are known or can be preparedin a simple manner by methods which are known in principle. For example,acyl-amino acid esters of the formula (II) are obtained when

a) amino acid esters of the formula (X) ##STR34## in which R⁴ representshydrogen (Xa) and alkyl (Xb) and

A, B and E have the abovementioned meaning are acylated withphenylacetic halides of the formula (XI) ##STR35## in which X, Y, Z andn have the abovementioned meaning and

Hal represents chlorine or bromine (Chem. Reviews 52 237-416 (1953));

or when acylamino acids of the formula (IIa) ##STR36## in which A, B, E,X, Y, Z and n have the abovementioned meaning and

R⁸ represents hydrogen are esterified (Chem. Ind. (London) 1568 (1968).

To obtain compounds of the structure (Ia), 1 to 2, preferably 1 to 1.3,moles of the phosphorus compound of the formula (III) are reacted permole of the compound (II) in preparation process A) at temperatures ofbetween -40° and 150° C., preferably between -10° and 110° C.

Suitable diluents which are optionally added are all inert, polarorganic solvents, such as ethers, amides, nitrites, alcohols, sulphides,sulphones, sulphoxides etc.

Diluents which are preferably employed are acetonitrile, dimethylsulphoxide, tetrahydrofuran, dimethylformamide and dimethyl sulphide.

Suitable acid-binding agents which are optionally added are customaryinorganic or organic bases, such as hydroxides or carbonates. Exampleswhich may be mentioned are sodium hydroxide, sodium carbonate, potassiumcarbonate and pyridine.

The reaction can be carried out at atmospheric pressure or underelevated pressure, preferably at atmospheric pressure. The products areworked up by methods which are customary in organic chemistry. The endproducts obtained are preferably purified by crystallization,chromatographic purification or by so-called "incipient distillation",that is to say, removal of the volatile constituents in vacuo.

Approximately 1 mole of sulphonyl chloride (IV) is reacted per mole ofstarting compound of the formula (II) in preparation process B), at 0°to 150° C., preferably at 20° to 70° C.

Suitable diluents which can optionally be added are all inert, polarorganic solvents, such as ethers, amides, nitrites, alcohols, sulphonesand sulphoxides.

Diluents which are preferably employed are dimethyl sulphoxide,tetrahydrofuran, dimethylformamide and dimethyl sulphide.

If, in a preferred embodiment, the enolate salt of the compound II issynthesized by adding strong deprotonating agents (such as, for example,sodium hydride or potassium tertiary butylate), the further addition ofacid-binding agents can be dispensed with.

If acid-binding agents are employed, then customary inorganic or organicbases are suitable, sodium hydroxide, sodium carbonate, potassiumcarbonate and pyridine being mentioned by way of example.

The reaction can be carried out at atmospheric pressure or underelevated pressure, it is preferably effected at atmospheric pressure.The products are worked up by customary methods.

If appropriate, preparation process B can be effected underphase-transfer conditions (W. J. Spillane et al., J. Chem. Soc. PerkinTrans I, (3) 677-9 (1982)). In this event, 0.3 to 1.5 moles of sulphonylchloride (IV), preferably 0.5 mole, are reacted per mole of startingcompound of the formula (II) at 0° to 150° C., preferably at 20° to 70°C. Examples of phase transfer catalysts which can be used are allquaternary ammonium salts, preferably tetraoctylammonium bromide andbenzyl-triethylammonium chloride. In this case, all unpolar inertsolvents can act as organic solvents, benzene and toluene beingpreferably employed.

Approximately 1 mole of isocyanate of the formula (V) is reacted permole of starting compound of the formula II in preparation processC.sub.α at 0° to 100° C., preferably at 20° to 50° C.

Suitable diluents which are optionally added are all inert organicsolvents, such as ethers, amides, nitriles, sulphones and sulphoxides.

If appropriate, it is possible to add catalysts to accelerate thereaction. Catalysts which can be very advantageously employed areorganotin compounds, such as, for example, dibutyltin dilaurate. Theprocess is preferably effected at atmospheric pressure.

Approximately 1 mole of carbamoyl chloride or thiocarbamoyl chloride ofthe formula (VI) is reacted per mole of starting compound of the formula(II) in preparation process C.sub.β at 0° to 150° C., preferably at 20°to 70° C.

Suitable diluents which are optionally added are all inert polar organicsolvents, such as ethers, amides, alcohols, sulphones and sulphoxides.

Diluents which are preferably employed are dimethyl sulphoxide,tetrahydrofuran, dimethylformamide and dimethyl sulphide.

If, in a preferred embodiment, the enolate salt of the compound II issynthesized by adding strong deprotonating agents (such as, for example,sodium hydride or potassium tertiary butylate), the further addition ofacid-binding agents can be dispensed with.

If acid-binding agents are employed, then customary inorganic or organicbases are suitable, sodium hydroxide, sodium carbonate, potassiumcarbonate and pyridine being mentioned by way of example.

The reaction can be carried out at atmospheric pressure or underelevated pressure, preferably under atmospheric pressure. The productsare worked up by customary methods.

Approximately 1 mole of chloromonothioformic ester or chlorodithioformicester of the formula (VII) is reacted per mole of starting compound ofthe formula (II) in preparation process D.sub.α at 0° to 120° C.,preferably at 20° to 60° C.

Suitable diluents which are optionally added are all inert polar organicsolvents, such as ethers, amides, alcohols, sulphones and sulphoxides.

Diluents which are preferably employed are dimethyl sulphoxide,tetrahydrofuran, dimethylformamide and dimethyl sulphide.

If, in a preferred embodiment, the enolate salt of the compound II issynthesized by adding strong deprotonating agents (such as, for example,sodium hydride or potassium tertiary butylate), the further addition ofacid-binding agents can be dispensed with.

If acid-binding agents are employed, then customary inorganic or organicbases are suitable, sodium hydroxide, sodium carbonate, potassiumcarbonate and pyridine being mentioned by way of example.

The reaction can be carried out at atmospheric pressure or underelevated pressure, preferably under atmospheric pressure. The productsare worked up by customary methods.

The equimolar amount, or an excess, of carbon disulphide is added permole of starting compound of the formula (II) in preparation processD.sub.β. This process is preferably effected at temperatures from 0° to50° C. and, in particular, at 20° to 30° C.

It is often expedient to first prepare the corresponding salt from thecompound of the formula (II) by adding a deprotonating agent (such as,for example, potassium tertiary butylate or sodium hydride). Thecompound (II) is reacted with carbon disulphide until the formation ofthe intermediate is complete, for example stirring for several hours atroom temperature.

The further reaction with the alkyl halide of the formula (VIII) ispreferably carried out at 0° to 70° C. and, in particular, at 20° to 50°C. In this process, at least the equimolar amount of alkyl halide isemployed.

The process is effected at atmospheric pressure or under elevatedpressure, preferably at atmospheric pressure.

Again, the products are worked up by customary methods.

When carrying out process (E) according to the invention, the startingsubstances of the formula (If) and the appropriate oxidant are employedin approximately equimolar amounts. The products are worked up by thecustomary methods.

Suitable oxidants for process (E) according to the invention are allreagents which oxidize sulphur, for example halogen such as chlorine andbromine, and their aqueous solutions, or alkali metal such as sodiumperoxide and potassium peroxide, salts of oxyhalogen acids such aspotassium chlorate, potassium bromate, sodium periodate and sodiumperborate, furthermore inorganic persalts such as potassiumpermanganate, potassium peroxodisulphate and potassiumperoxomonosulphate, but also H₂ O₂ in the presence of transition metalsalts such as sodium tungstenate and ammonium molybdate. Organicperoxides such as tert.-butyl hydroperoxide can furthermore be used, butalso organic peracids, such as peracetic acid, perpropionic acid andm-chloroperbenzoic acid (MCPBA).

Diluents which can be employed in process (E) according to the inventionare all solvents which are inert towards these compounds. The followingcan preferably be used: hydrocarbons, such as benzine, benzene, toluene,xylene and tetralin, furthermore halogenohydrocarbons such as methylenechloride, chloroform, chlorobenzene and dichlorobenzene, moreoverorganic acids such as acetic acid and propionic acid, and water.

If process (E) according to the invention is carried out in the presenceof a diluent, the reaction temperatures can be varied within asubstantial range. In general, the reaction temperatures are between-30° C. and +150° C., preferably between 0° C. and 100° C.

Process (E) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (F) according to the invention, the startingsubstances of the formula (If) and the appropriate oxidant are employedin approximately twice the equimolar amounts. However, it is alsopossible to employ the oxidant in a larger excess (up to 2 moles). Theproducts are worked up by the customary methods.

Suitable oxidants for process (F) according to the invention are allreagents which oxidize sulphur, for example halogen such as chlorine andbromine and their aqueous solutions, alkali metal peroxides such assodium peroxide and potassium peroxide, salts of oxyhalogen acids suchas potassium chlorate, potassium bromate, sodium periodate and sodiumperborate, furthermore inorganic persalts such as potassiumpermanganate, potassium peroxodisulphate and potassiumperoxomonosulphate, but also H₂ O₂ in the presence of transition metalsalts such as sodium tungstenate and ammonium molybdate. Organicperoxides such as tert.-butyl hydroperoxide can furthermore be used, butalso organic peracids such as peracetic acid, perpropionic acid andm-chloroperbenzoic acid (MCPBA).

Diluents which can be employed in process (F) according to the inventionare all solvents which are inert towards these compounds. The followingcan preferably be used: hydrocarbons such as benzine, benzene, toluene,xylene and tetralin, furthermore halogenohydrocarbons such as methylenechloride, chloroform, chlorobenzene and dichlorobenzene, moreoverorganic acids such as acetic acid and propionic acid, and water.

If process (F) according to the invention is carried out in the presenceof a diluent, the reaction temperatures can be varied within asubstantial range. In general, the reaction temperatures are between-30° C. and +150° C., preferably between 0° C. and 100° C.

Process (F) according to the invention is generally carried out underatmospheric pressure.

EXAMPLE 1 ##STR37##

11.1 g of3-(2,4,6-trimethyl-phenyl)-1,5-trimethylene-2,4-pyrrolidine-dione (0.04mol), 7 g (0.05 mol) of potassium carbonate and 0.5 g of (DABCO)(1,4-diazabicyclo 2.2.2!octane) (4.5 mmol) are suspended in 100 ml ofacetonitrile, 9.5 g (0.05 mol) of 2,2,2-trifluoroethylmethanethiochlorophosphonate are added at 20° C., and the mixture isstirred for one day at 20° C. The solid is subsequently filtered offwith suction, and the solution is evaporated on a rotary evaporator. Theresidue is filtered over silica gel (eluent: hexane:ethyl acetate=8:2).

8.9 g (52% of theory) of4-(2,2,2-trifluoroethoxy-methanethiophosphoryl)-3-(2,4,6-trimethylphenyl)-1,5-trimethylene-3-pyrrolin-2-oneare obtained, of melting point 109° C.

The following are obtained analogously:

    __________________________________________________________________________     ##STR38##                                                                    Example No.                                                                         X  Y  Zn  L R.sup.1                                                                              R.sup.2     A      B  E Physical                     __________________________________________________________________________                                                     data                         2     CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S OC.sub.2 H.sub.5                                                                     nC.sub.3 H.sub.7 S                                                                        (CH.sub.2).sub.3                                                                        H n.sub.D.sup.20 1.5662        3     CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                                                                         (CH.sub.2).sub.3                                                                        H n.sub.D.sup.20 1.5382        4     CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             SCH.sub.2C(CH.sub.3).sub.3                                                                (CH.sub.2).sub.3                                                                        H n.sub.D.sup.20 1.5636        5     CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OCH.sub.3   (CH.sub.2).sub.3                                                                        H n.sub.D.sup.20 1.5344        6     CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          (CH.sub.2).sub.3                                                                        H n.sub.D.sup.20 1.5507        7     CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.3 H.sub.7 -i                                                                       (CH.sub.2).sub.3                                                                        H Fp: 32° C.            8     CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.4 H.sub.9 -sec                                                                     (CH.sub.2).sub.3                                                                        H Fp: 89° C.            9     CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.4 H.sub.9 -iso                                                                     (CH.sub.2).sub.3                                                                        H                              10    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      OCH.sub.3   (CH.sub.2).sub.3                                                                        H Fp: 40° C.            11    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      OC.sub.3 H.sub.7 -i                                                                       (CH.sub.2).sub.3                                                                        H                              12    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      OC.sub.4 H.sub.9 -sec                                                                     (CH.sub.2).sub.3                                                                        H                              13    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      OC.sub.4 H.sub.9 -i                                                                       (CH.sub.2).sub.3                                                                        H                              14    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      SCH.sub.3   (CH.sub.2).sub.4                                                                        H n.sub.D.sup.20 1.5662        15    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      SC.sub.2 H.sub.5                                                                          (CH.sub.2).sub.4                                                                        H                              16    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      SC.sub.3 H.sub.7 -i                                                                       (CH.sub.2).sub.4                                                                        H                              17    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      SCH.sub.2 CHCH.sub.2                                                                      (CH.sub.2).sub.4                                                                        H                              18    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      SCH.sub.2 CCH                                                                             (CH.sub.2).sub.4                                                                        H                              19    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      SC.sub.4 H.sub.9 -sec.                                                                    (CH.sub.2).sub.4                                                                        H                              20    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      SC.sub.4 H.sub.9 -iso                                                                     (CH.sub.2).sub.4                                                                        H                              21    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                       ##STR39##  (CH.sub.2).sub.4                                                                        H                              22    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             SC.sub.3 H.sub.7 -n                                                                       (CH.sub.2).sub.4                                                                        H                              23    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                          (CH.sub.2).sub.4                                                                        H m.p.: 35° C.          24    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S                                                                                ##STR40##                                                                           OC.sub.2 H5 (CH.sub.2).sub.4                                                                        H                              25    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.3 H.sub.7 -i                                                                       C.sub.3 H.sub.7 -i                                                                   H  H                              26    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.3 H.sub.7 -i                                                                        ##STR41##                                                                           H  H                              27    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                       ##STR42##  (CH.sub.2).sub.4                                                                        H                              28    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S OC.sub.2 H.sub.5                                                                      ##STR43##  (CH.sub.2).sub.4                                                                        H                              29    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S n-C.sub.4 H.sub.9                                                                     ##STR44##  (CH.sub.2).sub.4                                                                        H                              30    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          (CH.sub.2).sub.4                                                                        H m.p. 42° C.           31    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      OCH.sub.3   (CH.sub.2).sub.4                                                                        H n.sub.D.sup.20 1.5757        32    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                          (CH.sub.2).sub.4                                                                        H m.p. 75° C.           33    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.3 H.sub.7 -i                                                                       (CH.sub.2).sub.4                                                                        H m.p. 32° C.           34    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                                  ##STR45##                                                                           H  H n.sub.D.sup.20 1.5515        35    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7 -i                                                                   CH.sub.3                                                                         H n.sub.D.sup.20 1.5076        36    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                           ##STR46##                                                                           H  H n.sub.D.sup.20 1.5505        37    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.3 H.sub.7 -i                                                                        ##STR47##                                                                           H  H n.sub.D.sup.20 1.5452        38    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7 -i                                                                   CH.sub.3                                                                         H n.sub.D.sup.20 1.5194        39    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      OCH.sub.3   C.sub.3 H.sub.7 -i                                                                   CH.sub.3                                                                         H n.sub.D.sup.20 1.5328        40    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7 -i                                                                   CH.sub.3                                                                         H n.sub.D.sup.20 1.5237        41    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                          (CH.sub.2).sub.3                                                                        H m.p. 42° C.           42    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O OC.sub.2 H.sub.5                                                                     SC.sub.3 H.sub.7 -i                                                                       (CH.sub.2).sub.3                                                                        H n.sub.D.sup.20 1.5392        43    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                         (CH.sub.2).sub.3                                                                        H                              44    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3                                                                             SCH(CH.sub.3)C.sub.2 H.sub.5                                                              (CH.sub.2).sub.3                                                                        H n.sub.D.sup.20 1.5412        45    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O C.sub.2 H.sub.5 O                                                                    SCH(CH.sub.3)C.sub.2 H.sub.5                                                              (CH.sub.2).sub.3                                                                        H n.sub.D.sup.20 1.5405        46    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O C.sub.2 H.sub.5 O                                                                    SC.sub.3 H.sub.7 -i                                                                       (CH.sub.2).sub.3                                                                        H                              47    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O CH.sub.3 O                                                                           SC.sub.3 H.sub.7 -i                                                                       (CH.sub.2).sub.3                                                                        H                              48    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O n-C.sub.4 H.sub.9 O                                                                  SC.sub.3 H.sub.7 -i                                                                       (CH.sub.2).sub.3                                                                        H                              49    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O CH.sub.3 O                                                                           SC.sub.4 H.sub.9 -sek                                                                     (CH.sub.2).sub.3                                                                        H                              50    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O n-C.sub.4 H.sub.9                                                                    SC.sub.4 H.sub.9 -sek                                                                     (CH.sub.2).sub.3                                                                        H                              __________________________________________________________________________

EXAMPLE 51 ##STR48##

2.58 g (0.01 mol) of3-(2,4,6-trimethyl-phenyl)-1,5-trimethylene-2,4-pyrrolidine-dione aresuspended in 20 ml of absolute dimethylformamide at room temperature. Tothis suspension there is added, in portions, 0.3 g of an 80% suspensionof sodium hydride in paraffin oil. Stirring is continued until evolutionof hydrogen has ceased. The mixture is then cooled to 10° C., and 1.6 g(0.014 mol) of methanesulphonyl chloride are added. Stirring iscontinued for 1 hour at room temperature, and the mixture is thenstirred in 100 ml of distilled water, the mixture is extracted (3 times)using methylene chloride, the organic phase is washed once using 40 mlof 5% strength hydrochloric acid and dried over sodium sulphate, and thesolvent is then stripped off in a rotary evaporator.

The crude product is chromatographed for purification (eluent mixture:ethyl acetate/cyclohexane 1:1)

Yield: 2.51 g (75%) of the title compound.

EXAMPLE 52 ##STR49##

2.71 g (0.01 mol) of3-(2,4,6-trimethyl-phenyl)-1,5-tetramethylene-2,4-pyrrolidine-dione aresuspended in 15 ml of toluene. 62 mg (0.2 mmol) of tetra-butylammoniumbromide, 0.86 g (0.005 mol) of diethylsulphamoyl chloride and 15 ml of30% by weight strength sodium hydroxide solution are added insuccession.

The vigorously stirred mixture is brought to 50° C. The reaction isallowed to proceed for 1.5 hours at this temperature. Then, 100 ml ofmethylene chloride and 100 ml of water are added, the organic phases areseparated, and the aqueous phase is re-extracted twice with methylenechloride. The combined organic phases are washed with water and driedover Na₂ SO₄.

The mixture is chromatographed for purification (eluent: ethylacetate/cyclohexane 1:3)

Yield: 400 mg (10%) of colourless, viscous oil

The following are obtained analogously:

    __________________________________________________________________________     ##STR50##                                                                    Example No.                                                                         X  Y  Zn  R.sup.3     A     B E Physical data                           __________________________________________________________________________    53    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3    (CH.sub.2).sub.3                                                                      H                                         54    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3    (CH.sub.2).sub.4                                                                      H m.p. 115-118° C.                 55    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR51##  (CH.sub.2).sub.4                                                                      H m.p. 163-165° C.                 56    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR52##  (CH.sub.2).sub.3                                                                      H m.p. 116-118° C.                 57    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR53##  (CH.sub.2).sub.3                                                                      H                                         58    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR54##  (CH.sub.2).sub.3                                                                      H m.p. 123-126° C.                 59    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CHCl.sub.2  (CH.sub.2).sub.3                                                                      H                                         60    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR55##  (CH.sub.2).sub.3                                                                      H                                         61    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR56##  (CH.sub.2).sub.4                                                                      H m.p. 151-154° C.                 62    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR57##  (CH.sub.2).sub.4                                                                      H                                         63    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        n-C.sub.4 H.sub.9                                                                         (CH.sub.2).sub.4                                                                      H                                         64    Cl CH.sub.3                                                                         6-Cl                                                                              CH.sub.3    (CH.sub.2).sub.3                                                                      H                                         65    CH.sub.3                                                                         CH.sub.3                                                                         5-CH.sub.3                                                                        CH.sub.3    (CH.sub.2).sub.3                                                                      H                                         66    Cl H  6-Cl                                                                              n-C.sub.4 H.sub.9                                                                         (CH.sub.2).sub.3                                                                      H                                         67    CH.sub.3                                                                         CH.sub.3                                                                         5-CH.sub.3                                                                        n-C.sub.4 H.sub.9                                                                         (CH.sub.2).sub.3                                                                      H                                         68    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        n-C.sub.12 H.sub.25                                                                       (CH.sub.2).sub.3                                                                      H m.p. 65° C.                      69    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        n-C.sub.12 H.sub.25                                                                       (CH.sub.2).sub.4                                                                      H m.p. 85-87° C.                   70    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR58##  (CH.sub.2).sub.4                                                                      H                                         71    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR59##  (CH.sub.2).sub.4                                                                      H                                         72    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                                   ##STR60##                                                                          H H                                         73    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                                   ##STR61##                                                                          H H                                         74    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        n-C.sub.4 H.sub.9                                                                          ##STR62##                                                                          H H                                         75    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        n-C.sub.4 H.sub.9                                                                          ##STR63##                                                                          H H                                         76    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR64##  (CH.sub.2).sub.3                                                                      H                                         77    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR65##  (CH.sub.2).sub.3                                                                      H                                         78    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR66##  (CH.sub.2).sub.4                                                                      H                                         __________________________________________________________________________

EXAMPLE 79 ##STR67##

2.71 g (0.001 mol) of3-(2,4,6-trimethyl-phenyl)-1,5-tetramethylene-2,4-pyrrolidine-dione aresuspended in 15 ml of absolute dimethylformamide, at room temperature.To this suspension there is added, in portions, 0.3 g (0.01 mol) of an80% suspension of sodium hydride in paraffin oil. Stirring is continueduntil the evolution of hydrogen has ceased. The mixture is then cooledto 10° C., and 1.23 g (0.013 mol) of dimethylcarbamoyl chloride areadded. The mixture is allowed to come to room temperature, warmed to 80°C., and stirred at this temperature for 1 hour. For working up, themixture is stirred into 35 ml of a 1% strength NaOH solution, and themixture is extracted 3 times using methyl chloride. The organic phase iswashed in succession with 15 ml of water and 15 ml of 5% strengthhydrochloric acid and then dried over sodium sulphate. After the dryingagent has been removed and the solvent has been stripped in a rotaryevaporator, the product is purified by chromatography. (Eluent: ethylacetate/cyclohexane 1:5)

Yield: 3.2 g (94%) of the title compound

The following are obtained analogously:

    __________________________________________________________________________     ##STR68##                                                                    Exaple No.                                                                          X  Y  Zn  L R.sup.4  R.sup.5  A  B  E Physical data                     __________________________________________________________________________    80    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3 CH.sub.3 (CH.sub.2).sub.4                                                                    H m.p. 188-189° C.           81    Cl H  6-Cl                                                                              O CH.sub.3 CH.sub.3 (CH.sub.2).sub.4                                                                    H m.p. 119-121° C.           82    Cl H  6-Cl                                                                              S CH.sub.3 CH.sub.3 (CH.sub.2).sub.4                                                                    H m.p. 158-161° C.           83    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O CH.sub.3 CH.sub.3 (CH.sub.2).sub.3                                                                    H                                   84    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S CH.sub.3 CH.sub.3 (CH.sub.2).sub.3                          85    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O CH.sub.2CHCH.sub.2                                                                     CH.sub.2CHCH.sub.2                                                                     (CH.sub.2).sub.3                                                                    H                                   86    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O CH.sub.3                                                                                ##STR69##                                                                             (CH.sub.2).sub.3                                                                    H                                   87    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O C.sub.3 H.sub.7 (n)                                                                    C.sub.3 H.sub.7 (n)                                                                    (CH.sub.2).sub.3                                                                    H                                   88    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O (CH.sub.2).sub.5  (CH.sub.2).sub.3                                                                    H                                   89    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S (CH.sub.2).sub.2O(CH.sub.2).sub.2                                                               (CH.sub.2).sub.3                                                                    H                                   90    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S (CH.sub.2).sub.5  (CH.sub.2).sub.3                                                                    H m.p. 112-116° C.           91    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                        (CH.sub.2).sub.3                                                                    H m.p. 112-116° C.           92    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S C.sub.2 H.sub.5                                                                         ##STR70##                                                                             (CH.sub.2).sub.3                                                                    H m.p. 106-110° C.           93    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S                                                                                ##STR71##        (CH.sub.2).sub.3                                                                    H                                   __________________________________________________________________________

EXAMPLE 94 ##STR72##

2.71 g (0.01 mol) of3-(2,4,6-trimethyl-phenyl)-1,5-tetramethylene-2,4-pyrrolidine-dione aresuspended in 20 ml of absolute dimethylformamide, at room temperature.To this suspension there is added, in portions, 0.3 g of an 80%suspension of sodium hydride in paraffin oil. Stirring is continueduntil the evolution of hydrogen has ceased.

3 ml of carbon disulphide are then added, and the mixture is stirred forthree hours at room temperature. Three ml of methyl iodide are added,and stirring is subsequently continued for 3 hours at room temperature.

For working-up, a mixture of 100 ml of water and 100 ml of methylenechloride is poured into the reaction mixture, and the aqueous phase isseparated off and re-extracted twice using methylene chloride. Thecombined organic phases are dried over sodium sulphate. After the dryingagent has been separated off and the solvent-has been fastened, theproduct is chromatographed. (Eluent: ethyl acetate/cyclohexane 4:1)

Yield: 1.5 g (41.5%) of the title compound

EXAMPLE 95 ##STR73##

2.58 g (0.01 mol) of3-(2,4,6-trimethyl-phenyl)-1,5-trimethylene-2,4-pyrrolidine-dione aresuspended in 20 ml of absolute dimethylformamide, at room temperature.To this suspension there is added, in portions, 0.3 g of an 80%suspension of sodium hydride in paraffin oil. Stirring is continueduntil the evolution of hydrogen has ceased.

1.5 ml (0.014 mol) of S-ethyl chlorothioformate are then slowly addeddropwise. When the addition has ended, stirring is continued for 1 hourat room temperature, and then 100 ml of water are added, the mixture isextracted 3 times using methylene chloride, and the organic phase iswashed once using 40 ml of 5% strength hydrochloric acid, dried andconcentrated.

Yield: 1.34 g (38.8%)

The following are obtained analogously:

    __________________________________________________________________________     ##STR74##                                                                    Example No.                                                                         X  Y  Zn  L M R.sup.6       A     B    E Physical                       __________________________________________________________________________                                                   Data                           96    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S O C.sub.2 H.sub.5                                                                             (CH.sub.2).sub.3                                                                         H                                97    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                                                             (CH.sub.2).sub.3                                                                         H oil                            98    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                                                             (CH.sub.2).sub.4                                                                         H oil                            99    CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S S C.sub.2 H.sub.5                                                                             (CH.sub.2).sub.4                                                                         H                                100   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S S i-C.sub.3 H.sub.7                                                                           (CH.sub.2).sub.4                                                                         H                                101   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S S n-C.sub.4 H.sub.9                                                                           (CH.sub.2).sub.4                                                                         H                                102   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S S                                                                                ##STR75##    (CH.sub.2).sub.4                                                                         H m.p. 140° C.            103   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S S CH.sub.2CHCH.sub.2                                                                          (CH.sub.2).sub.4                                                                         H                                104   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S S CH.sub.2CHCH  (CH.sub.2).sub.4                                                                         H m.p. 92-94° C.          105   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S S CH.sub.2CHCH.sub.2                                                                          (CH.sub.2).sub.3                                                                         H m.p. 103-105° C.        106   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S S C.sub.2 H.sub.5                                                                             (CH.sub.2).sub.3                                                                         H                                107   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        S S CH.sub.3                                                                                     ##STR76##                                                                          H    H m.p. 141-142° C.        108   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S n-C.sub.4 H.sub.9                                                                           (CH.sub.2).sub.3                                                                         H oil                            109   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.2 CHCH.sub.2CHCH.sub.3                                                       (CH.sub.2).sub.3                                                                         H oil                            110   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S                                                                                ##STR77##    (CH.sub.2).sub.4                                                                         H oil                            111   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S n-C.sub.4 H.sub.9                                                                           (CH.sub.2).sub.4                                                                         H oil                            112   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S t-C.sub.4 H.sub.9                                                                           (CH.sub.2).sub.4                                                                         H .sup.1 H-NMR (200                                                             MHz, CDCl.sub.3)                                                              δ = 1.37 (s,9H)                                                         4.28 (dd,1H)                                                                  4.4 (dd,1H)                                                                   6.85 (s,2H)                    113   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S i-C.sub.3 H.sub.7                                                                           (CH.sub.2).sub.4                                                                         H oil                            114   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.2 CHCH.sub.2CHCH.sub.3                                                       (CH.sub.2).sub.4                                                                         H oil                            115   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.3 C(CH.sub.2).sub.2                                                          (CH.sub.2).sub.4                                                                         H oil                            116   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.3 C(CH.sub.2)                                                                (CH.sub.2).sub.4                                                                         H m.p. 119° C.            117   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S s-C.sub.4 H.sub.9                                                                           (CH.sub.2).sub.4                                                                         H oil                            118   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S i-C.sub.5 H.sub.11                                                                          (CH.sub.2).sub.4                                                                         H oil                            119   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S n-C.sub.4 H.sub.9                                                                           (CH.sub.2).sub.3S                                                                        H oil                            120   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S                                                                                ##STR78##    (CH.sub.2).sub.2SCH.sub.2                                                                H oil                            121   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.3CH.sub.2                                                                    (CH.sub.2).sub.2SCH.sub.2                                                                H oil                            122   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S t-C.sub.4 H.sub.9                                                                           (CH.sub.2).sub.2SCH.sub.2                                                                H oil                            123   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S i-C.sub.3 H.sub.7                                                                           (CH.sub.2).sub.2SCH.sub.2                                                                H oil                            124   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.2 CHCH.sub.2CHCH.sub.3                                                       (CH.sub.2).sub.2SCH.sub.2                                                                H m.p. 135-136° C.        125   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.3 C(CH.sub.2).sub.2                                                          (CH.sub.2).sub.2SCH.sub.2                                                                H oil                            126   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S s-C.sub.4 H.sub.9                                                                           (CH.sub.2).sub.2SCH.sub.2                                                                H oil                            127   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S n-C.sub.4 H.sub.9                                                                            ##STR79##                                                                          H    H oil                            128   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S n-C.sub.4 H.sub.9                                                                           i-C.sub.3 H.sub.7                                                                   H    H oil                            129   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S t-C.sub.4 H.sub.9                                                                            ##STR80##                                                                          H    H m.p. 169-170° C.        130   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S i-C.sub.3 H.sub.7                                                                            ##STR81##                                                                          H    H m.p. 115-116° C.        131   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.2 CHCH.sub.2CHCH.sub.3                                                        ##STR82##                                                                          H    H oil                            132   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S t-C.sub.4 H.sub.9                                                                           i-C.sub.3 H.sub.7                                                                   H    H m.p. 160° C.            133   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S i-C.sub.3 H.sub.7                                                                           i-C.sub.3 H.sub.7                                                                   H    H m.p. 115° C.            134   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.2 CHCH.sub.2CHCH.sub.3                                                       i-C.sub.3 H.sub.7                                                                   H    H m.p. 70° C.             135   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.3 C(CH.sub.2).sub.2                                                          i-C.sub.3 H.sub.7                                                                   H    H m.p. 83-84° C.          136   CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        O S (CH.sub.3).sub.3 CCH.sub.2                                                                  i-C.sub.3 H.sub.7                                                                   H    H m.p. 103° C.            __________________________________________________________________________

The active compounds are suitable for combating animal pests, inparticular those of the class of the Arachuida and of the order of mites(Acarina) which are encountered in agriculture, in forestry, in theprotection of stored products and of materials, and in the hygienefield, and they have good plant tolerance and favourable toxicity towarm-blooded animals. They are active against normally sensitive andresistant species and against all or some stages of development. Theabovementioned pests include:

From the order of the Acarina, for example Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The active compounds according to the invention are not only activeagainst plant pests, hygiene pests and pests of stored products, butalso, in the veterinary medicine sector, against animal parasites(ectoparasites) such as scaly ticks, argasidae, scab mites andtrombidae.

They are active against normally sensitive and resistant species andstrains and against all parasitic and non-parasitic stages ofdevelopment of the ecto-parasites.

The active compounds according to the invention are distinguished by apowerful acaricidal activity. They can be employed with particularlygood success against mites which damage plants, such as, for example,against the common spider mite (Tetranychus urticae).

The active compounds according to the invention can furthermore be usedas defoliants, desiccants, agents for destroying broad-leaved plantsand, in particular, as weed-killers. By weeds, in the broadest sense,there are to be understood all plants which grow in locations-where theyare undesired. Whether the substances according to the invention act astotal or selective herbicides depends essentially on the amount used.

It is characteristic of the compounds according to the invention thatthey have a selective activity against monocotyledon weeds when used inthe pre- or post-emergence method, while being well tolerated by cropplants.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Monocotyleonous weeds of the genera: Eschinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledonous cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

Dicotyledonous cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum,. Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal combating of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for combating weeds in perennialcultures, for example afforestations, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings-and hopfields, andfor the selective combating of weeds in annual cultures.

In this context, the active compounds according to the invention notonly have an excellent action against harmful plants, but they are alsowell tolerated by important crop plants, such as, for example, wheat,cotton, soya beans, citrus fruit and sugar beet, and they can thereforebe employed as selective weed killers.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, suspensions, powders, foams, pastes,granules, aerosols, natural and synthetic materials impregnated withactive compound, fine capsules in polymeric substances and in coatingcompositions for seed, furthermore in formulations used with burningequipment, such as fumigating cartridges, fumigating cans, fumigatingcoils and the like, and also ULV cold-mist and warm-mist formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, liquefiedgases under pressure and/or solid carriers, optionally with the use ofsurface-active agents, that is emulsifying agents and/or dispersingagents and/or foam-forming agents. In the case of the use of water as anextender, organic solvents can, for example, also be used as auxiliarysolvents. As liquid solvents, there are suitable in the main: aromatics,such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics andchlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example petroleum fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water; by liquefied gaseous extenders orcarriers there are meant liquids which are gaseous at ambienttemperature and under atmospheric pressure, such as aerosol propellant,such as halogenohydrocarbons as well as butane, propane, nitrogen andcarbon dioxide; as solid carriers there are suitable: for example groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly-disperse silica, alumina and silicates; assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,corn cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be present in theircommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilants, acaricides, nematicides,herbicides or fungicides. The insecticides include for example, interalia, phosphoric esters, carbamates, carboxylic esters, chlorinatedhydrocarbons, phenylureas, and substances produced by microorganisms.

The active compounds according to the invention can furthermore bepresent in their commercially available formulations and in the useforms prepared from these formulations as a mixture with synergisticagents. Synergistic agents are compounds which increase the action ofthe active compounds, without it being necessary for the synergisticagent added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are applied in a customary manner appropriate for the useforms.

The active compounds which can be used according to the invention arealso suitable for combating mites, ticks etc. in the field of animalkeeping and livestock husbandry, it being possible to achieve betterresults, for example higher milk yields, higher weight, more beautifulanimal pelt, longer life, inter alia, by combating the pests.

The active compounds which can be used according to the invention areadministered in this field in a known maner, such as by oraladministration, in the form of, for example, tablets, capsules,drenches, granules, by dermal or external administration, for example inthe form of dipping, spraying, pouring-on and spotting-on, andpowdering, as well as by parenteral administration, for example in formof injection, as well as, furthermore, by the "feed-through" method.Besides, administration in the form of shaped articles (collar, ear tag)is also possible.

EXAMPLE A Phaedon Larvae Test

Solvent: 7 parts by weight of dimethylformamide/P compound: acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with mustard beetle larvae (Phaedon cochleariae), while theleaves are still moist.

After the specified period of time, the destruction in % is determined.100% means that all the beetle larvae have been killed; 0% means thatnone of the beetle larvae have been killed.

In this test, a superior activity compared with the prior art is shown,for example, by the following compounds of the preparation examples:(1), (2), (4), (59).

                  TABLE A                                                         ______________________________________                                        Phaedon larvae test                                                                                Active                                                                        Compound  Mortality                                                           Concentra-                                                                              in %                                           Active Compound      tion in % after 2 days                                   ______________________________________                                        Known from U.S. Pat. No. 4,985,063,                                           Ex. No. 249                                                                    ##STR83##           0.1        0                                              ##STR84##           0.1       50                                             according to the invention,                                                   Ex. No. 112                                                                   ______________________________________                                    

EXAMPLE B Plutella Test

Solvent: 7 parts by weight of dimethylformamide/P compound: acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with caterpillars of the diamond-back moth (Plutellamaculipennis) while the leaves are still moist.

After the specified period of time, the destruction in % is determined.100% means that all the caterpillars have been killed; 0% means thatnone of the beetle larvae have been killed.

In this test, a superior activity compared with the prior art is, shown,for example, by the following compounds of the preparation examples:(2).

                  TABLE B                                                         ______________________________________                                        Plutella test                                                                                      Active                                                                        Compound  Mortality                                                           Concentra-                                                                              in %                                           Active Compound      tion in % after 2 days                                   ______________________________________                                        Known from U.S. Pat. No. 4,985,063,                                           Ex. No. 249                                                                    ##STR85##           0.1        0                                              ##STR86##           0.1       67                                             according to the invention,                                                   Ex. No. 112                                                                   ______________________________________                                    

EXAMPLE C Nephotettix Test

Solvent: 7 parts by weight of dimethylformamide/P compound: acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Rice seedlings (Oryza sativa) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with larvae of the green leafhopper (Nephotettix cincticeps)while the seedlings are still moist.

After the specified period of time, the destruction in % is determined.100% means that all cicadas have been killed; 0% means that none of thecicadas have been killed.

In this test, a superior activity compared with the prior art is shown,for example, by the following compounds of the preparation examples:(1), (4), (53), (59).

                  TABLE C                                                         ______________________________________                                        Nepholettix test                                                                                    Active                                                                        Compound  Mortality                                                           Concentra-                                                                              in % after                                    Active Compound       tion in % 6 days                                        ______________________________________                                        Known from U.S. Pat. No. 5,045,560,                                           Ex. No. 682                                                                    ##STR87##            0.001      30                                            ##STR88##            0.001     100                                           according to the invention,                                                   Ex. No. 130                                                                   ______________________________________                                    

EXAMPLE D Spodoptera Test

Solvent: 7 parts by weight of dimethylformamide/P compound: acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with cater- pillars of the owlet moth (Spodoptera frugiperda),while the leaves are still moist.

After the specified period of time, the destruction in % is determined.100% means that all the caterpillars have been killed; 0% means thatnone of the caterpillars have been killed.

In this test, a superior activity compared with the prior art is shown,for example, by the following compounds of the preparation examples:(2).

EXAMPLE E Pre-Emergence Test

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of the active compound. It is expedient tokeep constant the amount of water per unit area. The concentration ofthe active compound in the preparation is of no importance, only theamount of active compound applied per unit area being decisive. Afterthree weeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control. The figuresdenote:

0%=no action (like untreated control)

100%=total destruction

In this test, a superior activity compared with the prior art is shown,for example, by the following compounds of the preparation examples:(1), (4), (53), (56), (58), (60).

                                      TABLE E1                                    __________________________________________________________________________    pre emergence test/greenhouse                                                 Active Compound     g/ha                                                                             ZEA MAYS                                                                            DIGITARIA SANGUINALIS                            __________________________________________________________________________    Known from U.S. Pat. No. 4,985,063,                                                               250                                                                              40    70                                               Ex. No. 249                                                                    ##STR89##                                                                    according to the invention,                                                                       250                                                                              0     90                                               Ex. No. 112                                                                    ##STR90##                                                                

    TABLE E2                                                                      __________________________________________________________________________    pre emergence test/greenhouse                                                                        TRITICUM                                                                            AGROPYRON                                                                            CYNODON                                                                             DIGITARIA                           Active Compound     g/ha                                                                             AESTIVUM                                                                            REPENS DACTYLON                                                                            SANGUINALIS                         __________________________________________________________________________    Known from U.S. Pat. No. 4,985,063,                                                               500                                                                              10    40     70    90                                  Ex. No. 243                                                                    ##STR91##                                                                    according to the invention,                                                                       500                                                                              0     70     100   100                                 Ex. No. 113                                                                    ##STR92##                                                                

    TABLE E3                                                                      __________________________________________________________________________    pre emergence test/greenhouse                                                                        ALOPECURUS                                                                            SETARIA                                                                            SORGHUM                                   Active Compound     g/ha                                                                             MYOSUROIDES                                                                           VIRIDIS                                                                            HALEPENSE                                 __________________________________________________________________________    Known from U.S. Pat. No. 4,985,063,                                                               500                                                                              40      50   30                                        Ex. No. 245                                                                    ##STR93##                                                                    according to the invention,                                                                       500                                                                              80      95   100                                       Ex. No. 117                                                                    ##STR94##                                                                

    TABLE E4                                                                      __________________________________________________________________________    pre emergence test/greenhouse                                                                             GOSSY-   DIGI- ECHINO-                                                                            PANI-    PORTU-                                       GLY-                                                                              PIUM                                                                              BROMUS                                                                             TARIA CLOA CUM POLI-                                                                              LACA                                         CINE                                                                              HIRSU-                                                                            SECAL-                                                                             SANGUIN-                                                                            CRUS-                                                                              MILIA-                                                                            GONUM                                                                              OLER-                Active Compound      g/ha                                                                             MAX.                                                                              TUM INUS ALIS  GALLI                                                                              CEUM                                                                              SPEC.                                                                              ACEA                 __________________________________________________________________________    Known from U.S. Pat. No. 5,045,560,                                                                250                                                                              30  10  50   80    70   90  0    0                    Ex. No. 682                                                                    ##STR95##                                                                    according to the invention,                                                                        250                                                                              0   0   80   100   100  100 70   100                  Ex. No. 130                                                                    ##STR96##                                                                

    TABLE E5                                                                      __________________________________________________________________________    pre emergence test/greenhouse                                                                         GLYCINE                                                                             DIGITARIA                                                                            ECHINOCLOA                                                                            LOLIUM                                                                             PANICUM                                                                              SETARIA              Active Compound      g/ha                                                                             MAX.  SANGUINALIS                                                                          CRUS-GALLI                                                                            PERENNE                                                                            MILIACEUM                                                                            VIRIDIS              __________________________________________________________________________    Known from U.S. Pat. No. 5,045,560,                                                                125                                                                              0     30     50      60   50     0                    Ex. No. 578                                                                    ##STR97##                                                                    according to the invention,                                                                        125                                                                              0     80     90      95   100    100                  Ex. No. 136                                                                    ##STR98##                                                                

Post-Emergence Test

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is so chosen that the particularamounts of active compound desired are applied in 2,000 of water/ha.After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control. Thefigures denote:

0%=no action (like untreated control)

100% =total destruction

In this test, a superior activity compared with the prior art is shown,for example, by the following compounds of the preparation examples:(1), (4), (53), (60), (85), (88).

                                      TABLE F1                                    __________________________________________________________________________    pre emergence test/greenhouse                                                                       BROMUS SETARIA                                                                            IPOMOEA                                                                             SINAPIS                               Active Compound    g/ha                                                                             SECALINUS                                                                            VIRIDIS                                                                            SPEC  ALBA                                  __________________________________________________________________________    Known from U.S. Pat. No. 4,985,063,                                                              2000                                                                              0      80   0    10                                    Ex. No. 249                                                                    ##STR99##                                                                    according to the invention,                                                                      2000                                                                             95     100  80    95                                    Ex. No. 112                                                                    ##STR100##                                                                   __________________________________________________________________________

                                      TABLE F2                                    __________________________________________________________________________    pre emergence test/greenhouse                                                                        TRITI-                                                                            GOSSY-       CYNO-                                                        CUM PIUM         DON                                                          AESTI-                                                                            HIRSU-                                                                             ALOPECURUS                                                                            DACTY-                                                                             LOLIUM                                                                              SETARIA                                                                            SORGHUM               Active Compound     g/ha                                                                             VUM TUM  MYOSUROIDES                                                                           LON  PERENNE                                                                             VIRIDIS                                                                            HALEPENSE             __________________________________________________________________________    Known from U.S. Pat. No. 4,985,063                                                                250                                                                              20  20    0      80    0     90   90                   Ex. No. 243                                                                    ##STR101##                                                                   according to the invention,                                                                       250                                                                               0   0   90      95   70    100  100                   Ex. No. 113                                                                    ##STR102##                                                                   __________________________________________________________________________

                                      TABLE F3                                    __________________________________________________________________________    pre emergence test/greenhouse                                                                          TRITICUM                                                                            GLYCINE                                                                            DIGITARIA                                                                             SETARIA                                                                            SORGHUM                      Active Compound       g/ha                                                                             AESTIVUM                                                                            MAX. SANGUINALIS                                                                           VIRIDIS                                                                            HALEPENSE                    __________________________________________________________________________    Known from U.S. Pat. No. 5,045,560                                                                  250                                                                              10    10   80      80   70                           Ex. No. 578                                                                    ##STR103##                                                                   according to the invention,                                                                         250                                                                               0     0   95      90   90                           Ex. No. 136                                                                    ##STR104##                                                                   __________________________________________________________________________

EXAMPLE G Tetranychus Test (OP-resistant)

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with watercontaining emulsifier to the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested with thecommon red spider mite or two-spotted spider mite (Tetranychus urticae)in all stages of development are treated by being dipped into thepreparation of the active compound of the desired concentration.

After the desired time, the mortality in % is determined. 100% meansthat all spider mites have been killed; 0% means that no spider miteshave been killed.

In this test, the following compounds show a superior activity comparedto the prior art:

                  TABLE G1                                                        ______________________________________                                        Tetranychus test (OP-resistant)                                                                    Active     Mortality                                                          Compound   in %                                                               Concentration                                                                            after                                         Active Compound      in %       7 days                                        ______________________________________                                        Known from U.S. Pat. No. 4,985,063,                                                                0.01       90                                            Ex. No. 243          0.001      80                                             ##STR105##                                                                    ##STR106##          0.01 0.001 95 95                                         according to the invention,                                                   Ex. No. 113                                                                   ______________________________________                                    

                  TABLE G2                                                        ______________________________________                                        Tetranychus test (OP-resistant)                                                                    Active     Mortality                                                          Compound   in %                                                               Concentration                                                                            after                                         Active Compound      in %       2 days                                        ______________________________________                                        Known from U.S. Pat. No. 4,985,063,                                                                0.01       40                                            Ex. No. 252                                                                    ##STR107##                                                                    ##STR108##          0.01       98                                            according to the invention,                                                   Ex. No. 116                                                                   ______________________________________                                    

                  TABLE G3                                                        ______________________________________                                        Tetranychus test (OP-resistant)                                                                    Active     Mortality                                                          Compound   in %                                                               Concentration                                                                            after                                         Active Compound      in %       7 days                                        ______________________________________                                        Known from U.S. Pat. No. 4,985,063,                                                                0.0001     70                                            Ex. No. 245                                                                    ##STR109##                                                                    ##STR110##          0.0001     95                                            according to the invention,                                                   Ex. No. 117                                                                   ______________________________________                                    

                                      TABLE G4                                    __________________________________________________________________________    Tetranychus test (OP-resistant)                                                                   Active Compound                                                                        Mortality in                                     Active Compound     Concentration in %                                                                     % after 7 days                                   __________________________________________________________________________    Known from U.S. 5,045,560                                                                         0.001    60                                               Ex. No. 682                                                                    ##STR111##                                                                    ##STR112##         0.001    98                                               according to the invention,                                                   Ex. No. 130                                                                   __________________________________________________________________________

                                      TABLE G5                                    __________________________________________________________________________    Tetranychus test (OP-resistant)                                                                     Active compound                                                                        Mortality in                                   Active compound       Concentration in %                                                                     % after 7 days                                 __________________________________________________________________________    Known from U.S. 5,045,560                                                                           0.001    35                                             Ex. No. 578                                                                    ##STR113##                                                                    ##STR114##           0.001    90                                             according to the invention,                                                   Ex. No. 136                                                                   __________________________________________________________________________

What is claimed is:
 1. A 3-arylpyrrolidine-2,4-dione derivative of theformula (I): ##STR115## in which A and B together with the nitrogen orcarbon atom to which they are bonded, form a 4-8 membered cyclic ringwherein A and B together represent --(CH₂)--₂₋₆ which is uninterruptedor interrupted by a sulfur atom or a sulfoxide or a sulfonyl group;Erepresents hydrogen, alkyl or alkoxyalkyl; X represents alkyl, halogenor alkoxy; Y represents hydrogen, alkyl, halogen, alkoxy orhalogenoalkyl; Z represents alkyl, halogen or alkoxy; n represents anumber from 0-3; R represents one of the groups: ##STR116## in which Lrepresents oxygen or sulfur in the case of group (a) or (c); or, in thecase of group (d), one of L and M represents oxygen and the otherrepresents sulfur or both L and M represent sulfur;R¹, R² and R³independently of one another represent alkyl, alkoxy, alkylamino,dialkylamino, alkylthio, alkenylthio, alkynylthio or cycloalkylthio,each of which is unsubstituted or substituted by halogen, or representphenyl, benzyl, phenoxy or phenylthio, each of which is unsubstituted orsubstituted by halogen, nitro, cyano, alkoxy, halogenoalkoxy, alkylthio,halogenoalkylthio, alkyl or halogenoalkyl; R⁴ and R⁵ independently ofone another represent hydrogen, or represent alkyl, alkenyl, alkoxy oralkoxyalkyl, each of which is unsubstituted or substituted by halogen,or represent phenyl or benzyl, each of which is unsubstituted orsubstituted by halogen, halogenoalkyl, alkyl or alkoxy; or R⁴ and R⁵together represent an alkylene radical which is uninterrupted orinterrupted by oxygen; R⁶ represents alkyl which is unsubstituted orsubstituted by halogen and which is uninterrupted or interrupted byoxygen, or represents phenyl which is unsubstituted or substituted byhalogen, halogenoalkyl or alkoxy, or represents benzyl which isunsubstituted or substituted by halogen, halogenoalkyl, alkyl or alkoxy,or represents alkenyl or alkynyl; or a pure enantiomeric form thereof.2. The 3-aryl pyrrolidine-2,4-dione derivative of the formula (I)according to claim 1, in whichE represent hydrogen or straight-chain orbranched C₁ -C₁₂ -alkyl or C₁ -C₈ -alkoxyalkyl X represents C₁ -C₆-alkyl, halogen or C₁ -C₆ -alkoxy, Y represents hydrogen, C₁ -C₆ -alkyl,halogen, C₁ -C₆ -alkoxy or C₁ -C₃ -halogenoalkyl, Z represents C₁ -C₆-alkyl, halogen or C₁ -C₆ -alkoxy, R¹, R² and R³ independently of oneanother represent C₁ -C₈ -alkyl, C₁ -C₈ -alkoxy, C₁ -C₈ -alkylamino,di-(C₁ -C₈)-alkylamino, C₁ -C₈ -alkylthio, C₂ -C₅ -alkenylthio, C₂ -C₅-alkinylthio or C₃ -C₇ -cycloalkylthio, each of which is optionallysubstituted by halogen, or represent phenyl, benzyl, phenoxy orphenylthio, each of which is optionally substituted by halogen, nitro,cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy, C₁ -C₄ --alkylthio, C₁-C₄ -halogenoalkylthio, C₁ -C₄ -alkyl or C₁ -C₄ -halogenoalkyl, R⁴ andR⁵ independently of one another represent C₁ -C₂₀ -alkyl, C₁ -C₂₀-alkoxy, C₂ -C₈ -alkenyl or C₁ -C₂₀ -alkoxy-C₁ -C₂₀ -alkyl, each ofwhich is optionally substituted by halogen, or represent phenyl which isoptionally substituted by halogen, C₁ -C₂₀ -halogenoalkyl, C₁ -C₂₀-alkyl or C₁ -C₂₀ -alkoxy, or represent benzyl which is optionallysubstituted by halogen, C₁ -C₂₀ -alkyl, C₁ -C₂₀ -halogenoalkyl or C₁-C₂₀ -alkoxy, or together represent a C₂ -C₆ -alkylene ring which isoptionally interrupted by oxygen, R⁶ represents C₁ -C₂₀ -alkyl which isoptionally substituted by halogen and which can be interrupted byoxygen, or represents phenyl which is optionally substituted by halogen,C₁ -C₂₀ -halogenoalkyl or C₁ -C₂₀ -alkoxy, or represents benzyl which isoptionally substituted by halogen, C₁ -C₂₀ -halogenoalkyl or C₁ -C₂₀-alkoxy, or represents C₂ -C₈ -alkenyl, or represents C₂ -C₅ -alkinyl,or a pure enantiomeric form thereof.
 3. The 3-arylpyrrolidine-2,4-dionederivative of the formula (I) according to claim 1, in whichA and Btogether with the nitrogen or carbon atom to which they are bonded forma 4 to 7-membered cyclic ring which can be interrupted by a sulphuratom, or by a sulphoxide or sulphonyl group, E represents hydrogen orstraight-chain or branched C₁ -C₁₀ -alkyl or C₁ -C₆ -alkoxyalkyl, Xrepresents C₁ -C₄ -alkyl, halogen or C₁ -C₄ -alkoxy, Y representshydrogen, C₁ -C₆ -alkyl, halogen, C₁ -C₄ -alkoxy or C₁ -C₂-halogenoalkyl, Z represents C₁ -C₄ -alkyl, halogen or C₁ -C₄ -alkoxy,R¹, R² and R³ independently of one another represent C₁ -C₆ -alkyl, C₁-C₆ -alkoxy, C₁ -C₆ -alkylamino, di-(C₁ -C₆)-alkylamino, C₁ -C₆-alkylthio, C₃ -C₄ -alkenylthio, C₂ -C₄ -alkinylthio or C₃ -C₆-cycloalkylthio, each of which is optionally substituted by halogen, orrepresent phenyl, benzyl, phenoxy or phenylthio, each of which isoptionally substituted by fluorine, chlorine, bromine, nitro, cyano, C₁-C₃ -alkoxy, C₁ -C₃ -halogen-alkoxy, C₁ -C₃ -alkylthio, C₁ -C₃-halogenoalkylthio, C₁ -C₃ -alkyl or C₁ -C₃ halogenoalkyl, R⁴ and R⁵independently of one another represent C₁ -C₂₀,-alkyl, C₁ -C₂₀ -alkoxy,C₂ -C₈ -alkenyl or C₁ -C₂₀ -alkoxy-C₁ -C₂₀ -alkyl, each of which isoptionally substituted by halogen, or represent phenyl which isoptionally substituted by halogen, C₁ -C₅ -halogenoalkyl, C₁ -C₅ -alkylor C₁ -C₅ -alkoxy, or represent benzyl which is optionally substitutedby halogen, C₁ -C₅ -alkyl, C₁ -C₅ -halogenoalkyl or C₁ -C₅ -alkoxy, R⁶represents C₁ -C₂₀ -alkyl which is optionally substituted by halogen andwhich can be interrupted by oxygen, or represents phenyl which isoptionally substituted by halogen, C₁ -C₅ -halogenoalkyl or C₁ -C₅-alkoxy, or represents benzyl which is optionally substituted byhalogen, C₁ -C₅ -halogenoalkyl or C₁ -C₅ -alkoxy, or a pure enantiomericform thereof.
 4. A 3-arylpyrrolidine-2,4-dione derivative of the formula(I) according to claim 1, in whichA and B together with the nitrogen orcarbon atom to which they are bonded form a 5-6-membered cyclic ringwhich can be interrupted by a sulphur atom or by a sulphoxide orsulphonyl group, E represents hydrogen or straight-chain or branched C₁-C₈ -alkyl or C₁ -C₄ -alkoxyalkyl, X represents methyl, ethyl, propyl,i-propyl, fluorine, chlorine, bromine, methoxy or ethoxy, Y representshydrogen, methyl, ethyl, propyl, i-propyl, butyl, i-butyl, tert.-butyl,fluorine, chlorine, bromine, methoxy, ethoxy or trifluoromethyl, Zrepresents methyl, ethyl, i-propyl, butyl, i-butyl, tert.-butyl,fluorine, chlorine, bromine, methoxy or ethoxy, R¹, R² and R³independently of one another represent C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁-C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino or C₁ -C,-alkylthio, each ofwhich is optionally substituted by fluorine or chlorine, or representphenyl, benzyl, phenoxy or phenylthio, each of which is optionallysubstituted by fluorine, chlorine, bromine, nitro, cyano, C₁ -C₂-alkoxy, C₁ -C₄ -fluoroalkoxy, C₁ -C₂ -chloroalkoxy, C₁ -C₂ -alkylthio,C₁ -C₂ -fluoroalkylthio, C₁ -C₂ -chloroalkylthio or C₁ -C₃ -alkyl, R⁴and R⁵ independently of one another represent each of which isoptionally substituted by fluorine, chlorine, bromine, C₁ -C₂₀ -alkyl,C₁ -C₂₀ -alkoxy, C₂ -C₈ -alkenyl or C₁ -C₂₀ -alkoxy-(C₁ -C₂₀)alkyl, orrepresent phenyl which is optionally substituted by fluorine, chlorine,bromine, C₁ -C₂₀ -halogenoalkyl, C₁ -C₂₀ -alkyl or C₁ -C₂₀ -alkoxy, orrepresent benzyl which is optionally substituted by fluorine, chlorine,bromine, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl or C₁ -C₄ -alkoxy, R⁶represents C₁ -C₂₀ -alkyl which is optionally substituted by fluorine,chlorine or bromine and which can be interrupted by oxygen, orrepresents phenyl which is optionally substituted by fluorine, chlorine,bromine, C₁ -C₄ -halogenoalkyl or C₁ -C₄ -alkoxy, or represents benzylwhich is optionally substituted by fluorine, chlorine, bromine, C₁ -C₄-halogenoalkyl or C₁ -C₄ -alkoxy, or a pure enantiomeric form thereof.5. The 3-arylpyrrolidine-2,4-dione derivative according to claim 1,having the formula ##STR117##
 6. The 3-arylpyrrolidine-2,4-dionederivative according to claim 1, having the formula ##STR118##
 7. The3-arylpyrrolidine-2,4-dione derivative according to claim 1, having theformula ##STR119##
 8. The 3-arylpyrrolidine-2,4-dione derivativeaccording to claim 1, having the formula ##STR120##
 9. The3-arylpyrrolidine-2,4-dione derivative according to claim 1, having theformula ##STR121##
 10. An insecticidal composition comprising aninsecticidally effective amount of a 3-arylpyrrolidine-2,4-dionederivative according to claim 1 and a carrier.
 11. An acaricidalcomposition comprising an acaricidally effective amount of a3-arylpyrrolidine-2,4-dione derivative according to claim 1 and acarrier.
 12. A herbidial composition comprising a herbicidally effectiveamount of a 3-arylpyrrolidine-2,4-dione derivative according to claim 1and a carrier.
 13. A method of combating insects comprising applying tothe weeds or their environment an insecticidally effective amount of a3-arylpyrrolidine-2,4-dione derivative according to claim
 1. 14. Themethod according to claim 13, wherein the 3-arylpyrrolidine-2,4-dionederivative is selected from the group consisting of ##STR122##
 15. Amethod of combating acarides comprising applying to the acarides ortheir environment an acaricidally effective amount of a3-arylpyrrolidine-2,4-dione derivative according to claim
 1. 16. Themethod according to claim 15, wherein the 3-arylpyrrolidine-2,4-dionederivative is selected from the group consisting of ##STR123##
 17. Amethod of combating weeds comprising applying to the weeds or theirenvironment a herbicidally effective amount of a3-arylpyrrolidine-2,4-dione derivative according to claim
 1. 18. Themethod according to claim 17, wherein the 3-arylpyrrolidine-2,4-dionederivative is selected from the group consisting of ##STR124##
 19. The3-arylpyrrolidine-2,4-dione derivative according to claim 1, wherein Aand B together represent --(CH₂)₃ -- or --(CH₂)₄ --.
 20. The3-arylpyrrolidine-2,4-dione derivative according to claim 1, wherein Aand B together represent an uninterrupted 4-8 membered cyclic ring.